Anonymous Mailbag

Rejoice, it’s anonymous mailbag Tuesday.

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Okay, here we go:

“When I was 10 years old I was a little white boy who dressed as Steve Urkel in blackface for Halloween. Guess what, no one gave a shit or called me racist or anything. Should I be forbidden from ever being a CEO or running for office or having any sort of public life whatsoever?”

You clearly lived in Megyn Kelly’s neighborhood.

Just to be safe I’d probably destroy the photos — if they exist — and claim this email never happened.

More seriously, I think because you’re a kid your parents would be blamed for this, not you. So if your parents were public figures I have zero doubt that this would be a major national story and they’d get raked over the coals for this behavior.

I mean, think about it, can you imagine if photos of Donald Trump, Jr. wearing blackface dressed as Michael Jackson for Halloween when he was seven or eight years old, suddenly emerged?

The news media would lose its mind in masturbatory excess.

Most people wouldn’t blame Donald Trump, Jr. everyone would blame his dad, even if, as might be the case, Jr. wasn’t living with his dad and Trump had no idea what his son’s Halloween costume was that year.

Having said all of this, INTENT MATTERS.

When you’re a kid you typically dress up as someone you idolize. The entire purpose of Halloween, especially for young kids, is to dress up as people you like, admire, or wish you were.

I’ve never seen anyone wear blackface at any Halloween party (or anywhere else for that matter), but just because something was insanely racist at the turn of the century doesn’t mean your average kid today at Halloween is intentionally trying to offend others by dressing up as his favorite black superhero. I have a wild idea — intent matters.

There’s a difference, to me, between the picture in the Virginia governor’s medical school yearbook — which was the use of blackface that was clearly intended to be racist –, between a college kid dressing up as a black singer to pay homage at a party, which was clearly stupid, but again, intended to be complimentary, and between an elementary school kid dressing up on Halloween as Steve Urkel, which was an act undertaken, probably, with zero intent to be racist.

It seems to me that social media has led to a complete inability to understand nuance and analyze intent. There’s no room for middle ground or for giving anyone the benefit of the doubt or for considering surrounding circumstances. All actions are not identical and everything in this country is not black or white. (Either in a literal or figurative context).

That’s especially the case in America today when there are so many people from so many different ethnic backgrounds. Do you think your average Asian, European, Hispanic or even African immigrant knows the history of blackface in America today?

Think about this, if one of their young kid’s was a fan of the Black Panther and they didn’t have the mask and instead covered his face in black make up, would you think they were intentionally being racist or that the kid wanted to dress up like the Black Panther and they didn’t know the history of blackface in the country? (The New York Times, setting an all time record for superhero wokeness, even wrote a front page article asking if white kids could buy black panther costumes. Seriously.)

If you have trouble thinking about this situation, imagine that you suddenly moved to India and were celebrating a major holiday in their country for one of the first times. Isn’t it possible that you could do something that was considered racist or culturally inappropriate in their country and have had no idea you were doing so? Of course it is. You wouldn’t know your behavior was considered offensive unless someone told you.

I believe that right now we’re in a modern day racial McCarthy era where people just toss out accusations of racism and we’ve lost all ability to use reasonable intellect or analysis to consider whether the behavior is actually racist.

When everything is racist then that also means nothing is racist.

In fact, when you argue everything is racist, you devalue actual racism, creating a perpetual boy who cried wolf scenario. When actual racism occurs, there are no allies left to combat it because they’ve all stopped paying attention due to the baseless accusations of the past.

“My girlfriend and I have been together for 3+ years, and the past 6 months or so, I’ve noticed that there’s been a decreased effort on her part in regards to the sexiness factor. By that I mean it’s been a lot (90%+) of sweatpants, hair up, no make-up, lack of grooming in the nether regions, etc. She is currently in the middle of med school, which I obviously understand is stressful and physical appearances are not of the utmost concern at this point. At the same time, I don’t want this to become a permanent thing, even after she finishes school. To be clear, I’m certainly not expecting her to dress to the nines every day, but I feel like a little effort can go a long way.
What’s the play to ask her to try a little harder without coming off like a selfish dick?”
Take her out on an expensive Valentine’s dinner where everyone else will be dressed well in the restaurant.
Women, especially women who are in long term relationships, dress to impress other women more than they dress to impress men.
If you want your girlfriend to step up her hotness game, you need to step up the game of the places you’re taking her out. Make her want to show off for you, but, more importantly, for the rest of the people there.
Every man who has ever been in a relationship very long gets asked this question over and over again and never knows what to say, “What are people going to be wearing there?”
By “people” your wife or girlfriend means “other women.”
Because odds are no one cares what the guy wears. I can wear jeans and a button down shirt with a jacket to pretty much every social event I’d ever go to and no one will even blink. But the subtle variations in what women wear to events can be astounding.
I’d guess your girlfriend is following the social cues of the other women in med school. They’re all spending so much time studying they aren’t worried about their physical appearance as much as the same women might have been when they were undergrads in college.
Due to the incredible stress and competition in med school your girlfriend just doesn’t have the time to spend on other things right now.
So rather than being an asshole boyfriend have you thought about paying for her to go to a spa or paying for her to get her hair done and get a manicure after a stressful exam, when you know she has a day or two to come up for air? The bonus here is you seem like a great boyfriend, but you’re also getting something you want without being a dickhead about it.
See, everybody wins.

“When you’re having a heart attack, stroke, or you just dropped dead, I’m the guy who you call to take care of you.

Right now I am a 911 paramedic and I make more money than a seasoned firefighter at a big city department. With that being said, I want to be a fireman.

It’s competitive which means I will need to apply to several cities which would mean I would have to move my wife and daughter from our current home. I would also have to sell our house that we just purchased. My wife has said no if it means we have to move away from our current home. She wants to stay close to family. I understand wanting to stay close to family, but isn’t this what people do? They relocate so they can further advance in their career. Is this foolish of me for wanting to do this? Is my wife right? She says I am in the wrong and selfish. What do you think?” 

I mean, you want to move your family to a new city so you can make less money in a new career. In order to do that you’d have to sell the new house you just purchased.

Did you not realize your fireman desire before you bought the house?

I feel like I’m talking to a kid here who says he has to go to the bathroom ten minutes after we just started on a long drive. How many times has every parent said, “But I just asked if you had to go to the bathroom ten minutes ago and you said you didn’t!”

Anyway, I think your wife is correct here, you’re being selfish.

Now, to be fair to you, sometimes people need to pursue a different line of work to be more happy in their life. But your job doesn’t change that much in the grand scheme of things here — you’re still the guy people call when emergencies happen.

I don’t blame your wife, I wouldn’t want to uproot the life of my family for you to switch to this job either, especially not if meant leaving her family and moving out of a house you guys just bought.

You also didn’t mention her job in your email at all. Does she work? That factors in here as well since in addition to moving away from her family and selling the house she might have to find a new job as well.

Honestly, your email is so focused on yourself it’s hard to come to any conclusion other than this is a selfish move on your part.

I agree with your wife.

“King Solomon, I need some advice about my relationship with my girlfriend and her family. 

Every major holiday, we go to visit and stay with her family and after 2 or 3 days I snap at one of her parents or uncles/aunts because I can’t take it any longer. 

They’re extremely overbearing to the point of driving me insane, loud as hell–life on mars is more likely than them discovering inside voices, and I just don’t like them. If I wasn’t dating my girlfriend, I wouldn’t spend one moment with anyone in her family. 

My girlfriend wants her parents to live with us when they retire (it’s how their culture does it) but I can’t spend three days with them so how would I survive years on end? Also, I do not want her parents taking care of or influencing our future children because they don’t speak English nor a useful language like Spanish, French, etc. Moreover, I don’t want my kids to pick up their cultural habits, most of which in the US and a lot of other countries would be considered rude and unacceptable. 

We’ve been together nearly 3 years-I’m almost 28 and she’s 31 so the biological clock is ticking and her entire family nags every month and every visit about when we’re getting married and how some other person in the small town of 400 just got married or had another kid.  

My girlfriend doesn’t like that I don’t want to visit her family let alone have them live with us. She says it’s not a deal breaker, but I’m not sure I believe her. 

What should I do? Do I suck it up and spent several miserable days with her family every few months? Is this a fight I should fight? 

I’m not trying to be a martyr nor do I want to tear her away from her family…but should we break up to please her and her family? She can see her parents without me being so angry, she can get married sooner rather than later, her parents can live with her later, help around the house, etc. 

What would be your advice?”

Man, your girlfriend needs to break up with you, not vice versa.

You sound like a total asshole.

I have no idea what your girlfriend’s family is like, but talking loudly and being boisterous during the holidays is pretty common family behavior. The bigger issue, however, is that you say her family doesn’t speak a “useful language like French or Spanish.”

What an absurd statement to make.

I have no idea what language they speak — I’m guessing they are Asian, maybe, because you eliminated French and Hispanic people from consideration based on language choice, but they could be another ethnicity — but the fact you don’t want your own kids to interact with their grandparents because of their culture is just a massive red flag here. Again, reading this email it seems like you’re telling on yourself — your girlfriend’s family seems fine and you seem like a total dickhead.

While I think you should break up with your girlfriend because your attitude doesn’t lead to a good long range fit, I think the better solution is she needs to break up with you.

I’m not sure if you can do better than her, but I’m pretty much certain she can do better than you.

“So I’ve asked a few of my girlfriends for advice but I need a “no bullshit” response so I’m coming to you. I have been talking to this guy for about 4 months now. Back story is he lives about 3.5 hours away for military pilot training, met online and have hung out once in that period of time since his schedule is very busy. We talk almost everyday and have good conversation both in person and texting.

I want to ask him what he sees happening from this but I don’t want to sound crazy since we have only met once and he is a few years younger than me. I’m not looking for a full commitment, just to know he can see us dating in the future. I am afraid to scare him away because why ruin something good. What would you do in my situation? When is the appropriate time into talking with someone to ask what the deal is? Help please!”

Did you sleep together the one time you saw each other?

That matters quite a bit here.

If you did sleep with him then he may just consider you a casual fling and have been interacting with you because he’s pursuing easy sex, if you didn’t sleep with him then he’s expending a lot of effort to keep up the lines of communication with you.

Regardless, I don’t think there’s anything at all wrong with telling him you’re interested in something more serious than what you have right now.

But I think you have to prepare yourself for him not wanting anything different than whatever it is you have right now.

I don’t think there’s ever anything wrong with expressing your true feelings in a relationship and there’s certainly nothing wrong with wanting more than you have right now. But your email makes it clear you’re afraid that he might not feel the same way you do and don’t want to risk hearing him say it.

I get that.

But is having some certainty from him, even if it’s not what you want to hear, not better than living in constant uncertainty about what he wants? I think so. Because once you know his answer you can decide whether to invest more time in him or not, which is ultimately the decision every person who has ever been in a relationship has to make.

Good luck.

“I recently had sex with my girlfriend for the first time and it was great. We have had sex several times since then and she has said that she doesn’t want our relationship to be just about sex, which is reasonable. But she constantly teases me with sexual innuendo. How should I take that and what should I do?”

First, congrats on the sex.

Second, welcome to the rest of your life.

Every woman who has ever been born wants to make sure a “relationship isn’t just about sex” while simultaneously taking advantage of how much men crave sex by making us do things we wouldn’t otherwise do just because of our pursuit of that sex in that relationship.

She wants you to want her for more than sex while simultaneously knowing she can take advantage of how much you want to have sex with her.

And that’s with premarital sex being commonplace!

Can you imagine how much women used the allure of sex when having sex before marriage didn’t happen very often? Those poor dudes.

I can’t even imagine how rough their lives must have been.

They got excited when they saw an ankle!

An ankle!

So things could be worse.

Send your questions to, anonymity guaranteed.

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.